


The Quest to Take Sam's Disco Stick

by therealfroggy



Category: Supernatural
Genre: Established Dean Winchester/Sam Winchester, First Time Bottom Dean Winchester, Friends to Lovers, M/M, Multi, Size Difference, Size Kink, Threesome, Threesome - M/M/M
Language: English
Status: Completed
Published: 2020-05-16
Updated: 2020-05-16
Packaged: 2021-03-02 16:53:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,539
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24220126
Author URL: https://archiveofourown.org/users/therealfroggy/pseuds/therealfroggy
Summary: Dean always tops when they fuck, out of pure necessity. Yeah, go ahead, laugh: Dean Winchester can't take Sam Winchester's dick. It's too friggin' big. That is... it was, until Castiel came along.The Quest to Take Sam's Disco Stick, or, that time when Dean fell in love with an angel as well as his brother, and it turned out angel mojo is good for more than zapping you places.Established Dean/Sam turning into Dean/Sam/Castiel. Just 27 pages (yikes) of wholesome sexy times with the boys, no angst, some dick jokes. Because that's what we need in these hard times.
Relationships: Castiel/Dean Winchester/Sam Winchester, Dean Winchester/Sam Winchester
Comments: 2
Kudos: 167





	The Quest to Take Sam's Disco Stick

Dean always tops when they fuck. Sam insists it's not a big deal, that he likes it this way, but Dean can't help but wonder.

When they were younger, Dean always topped because he was the older brother. Since that first time when Sammy, seventeen and desperate and unable to hold out against the lust he felt for his brother, had crawled into Dean's lap and begged him for it, Dean has always taken care of his little brother. Their relationship has never been entirely sane and definitely not morally sound from an outside perspective, but Dean has always taken care of Sam and Sam has always been adamant that he likes it this way.

Now that they're older, and Sam is freakishly huge, it's actually more about physical concerns. Dean was mortified the first time they tried to switch and it turned out he was unable to take Sam like that; his younger brother is perversely proportional and no matter how long Dean tried, he just couldn't stop whimpering in pain when Sam tried entering him. Didn't matter that Sam had been slowly fingering him open for fifteen fucking minutes; Sam's disco stick was just too much for Dean to handle.

Yeah, go ahead, laugh, Dean Winchester can't take Sam Winchester's dick. It's too friggin' big.

Sam still insists that it doesn't matter, that he's happy being on the receiving end of that stick. He obviously enjoys it, or Dean wouldn't let him do it, but the blond man can't stop thinking that if he was man enough, he could let Sammy – his little Sammy, who is not really little in any conceivable nuance of the word – enjoy it from the other end, too.

They tried twice, and it hurt too damn much, so Dean cried uncle and admitted that he just couldn't do it. Sam kissed him and told him not to worry about it, and their fucked up relationship is still fucked up, but no more so than it always has been. What with them being brothers and all.

Until Castiel comes along, of course.

Sam noticed Dean looking at Cas long before Dean was ready to admit to himself that he felt things for the angel, but knowing how unbearably pissy Dean would get, Sam kept quiet. Until the day when Dean, forced to admit his feelings to himself when he got hard over seeing Cas shirtless, came to Sam to confess.

Dean looked Sam in the eyes and stuttered that he felt like a dick, but he wanted Cas, and could Sam please stop being so damn good to him and just ditch him already? Sam's patience and understanding was making Dean feel like an even bigger dick.

Sam kissed him and told him to invite Cas to their motel room.

So that's where they are, now; Dean has bought booze and Sam, neat freak, has bought condoms and fancy lube, and they're sitting side by side on the king size bed while Dean prays for Castiel.

“Hey, Cas,” he starts, gruff and hesitant. “Uh, yeah, so, if you can hear me, come on down. Or something. I mean... if you got time.”

A heartbeat later, the sound of wings announce Castiel's arrival. Sam and Dean both look up to find the angel, solemn and focused, standing in front of them.

“Dean. I heard your prayer,” Castiel greets the older Winchester. Then he turns to Sam. “Hello, Sam. You look untroubled. This is unusual for you.”

Sam laughs. “Yeah, well, I've got a lot to look forward to.”

It takes them a little time to convince Castiel to stay for a social call, but eventually the angel accedes and looks around him uncertainly. Dean hands him a drink and once he's downed that, Sam – who's always got Dean's back – goes up to Dean and kisses him deeply in front of their visitor.

Castiel cocks his head even further to the side. “I thought humans were usually secretive and ashamed about incestuous relationships.”

“But you knew we had one,” Sam observes, turning to face the angel.

“Yes,” Castiel confirms. “I have watched you.”

Dean splutters. “Dude! That's wrong! What is it with you wing nuts, spying on people? Perv!”

“Dean,” Sam says, annoyed. “Trying to get him to stay, remember?” Then the younger brother holds out a hand to Castiel. “Cas?”

Dean takes a deep breath. “Please, Cas. I... I want you.”

Castiel's brow contracts in a frown. “You do? I did not expect that.”

“Well?” Dean asks, annoyed. What, was _Sam_ more likely to want the angel than Dean, whose soul Cas had saved? For whom Castiel had done everything?

“While I would very much like to participate in your intimate activities, I have no experience in these matters,” Castiel answers calmly. “I do not usually observe humans very closely during these moments; it is impolite. And angels are not... anatomically comparable when we engage in these activities.”

“But you've watched us?” Sam asks, taking a step closer to Castiel.

“Yes. You are of special import. I observed you closely before I helped you become invisible to us,” the angel confirms.

“So you know what we like,” Sam presses.

Castiel looks confused. “I... find it hard to separate between your appreciation of each other and your appreciation of the physical acts in which you are engaged. I also find myself affected by your mutual appreciation in ways which make it hard to make objective observations.”

Dean chuckles. “You mean you got off on watching us have sex. Pervert.”

“But we'll help,” Sam offers, giving Dean a dirty look. Shut up, you're ruining our clever seduction plan. “We'll show you everything you need to know.”

Castiel offers them a rare smile. “Then yes, I would very much like to share in your incestuous relationship.”

Dean groans. “Would you not call it that?”

“But that is what it is,” Castiel says, clearly puzzled.

“Never mind, just shut up,” Dean growls, and closes in on the angel. “Seriously? You want to do this?”

“Yes. Were you not sincere in inviting me?” Castiel asks, completely serious.

“No, no, of course we were,” Sam soothes. “Dean, help him out of his coat, dude.”

When Castiel looks at him with inviting expectation, Dean rushes over to grab the boring, tan lapels. He leans in and crushes their lips together, and tastes Cas for the first time.

He tastes like lightning.

Cas just stands there, kissing back, even when Dean and Sam begin stripping him. The angel lets himself be undressed, quietly, just watching the brothers intently. When he is finally naked, he looks expectantly up at Dean, then at Sam.

“Well?”

“Get on the bed,” Dean growls. “Sam, show him how to get himself ready.”

The brothers both strip, and Castiel's eyes light up with interest. He watches them closely, and then his focus shifts to Sam as the younger brother joins him on the bed. Sam hands over a bottle of lube.

“Use plenty of this. Here, let me...”

And Sam coats his fingers in lube, then reaches down between Cas' legs and rubs a finger slowly over that clenched muscle where Dean wants to bury himself. Cas sighs happily and spreads his legs wider.

“Yes, that feels very pleasant. Which one of you will sodomize me?”

Dean snorts. “How do you even... You know what, Cas, just stop talking. Your dirty talk is seriously off. And I'll be doing the sodomizing here.”

“I think we'd better get you on your side for this,” Sam says, his voice husky and low. “Since you're a first-timer.”

Cas, lying on his side with his left leg bent up, trustingly places his head on Sam's arm when Sam presses in close behind him. The younger Winchester seems to dwarf the angel as his large hand searches between Castiel's thighs. Castiel's vessel is not a diminutive man but even he seems slight lying next to Sam Winchester.

“Oh,” Cas mutters when Sam's fingers slide into him. “Oh, that is... strange.”

“You tell me to stop, I stop, okay?” Sam says earnestly. “Cas, really, we're not doing anything you don't like.”

“I like this,” Castiel says immediately. “It is only strange, that... that something so... that this should feel so pleasant.”

“Take a deep breath for me, okay?” Sam mutters and kisses Castiel's neck.

Cas frowns. “I do not need to breathe.”

“No, but your body will relax if you do,” Sam explains. “Deep breath, that's it, now slowly out.”

As Castiel exhales, Sam slides three fingers into him. Dean, watching from the foot of the bed, is keeping his clenched fists well away from himself. The sight of Cas in his brother's arms is too much all on its own; if he touches himself, he's going to come all over that ugly duvet and the fun will be over.

“I feel very close to you,” Cas says, sounding surprised. “Sam, I have not felt quite so profoundly bound to you as I have your brother, but now I... I feel we are much closer than before.”

“Good to hear,” Sam smiles into the skin of Castiel's shoulder. “Hey, Cas, how you doing?”

“I am ready,” is the prompt reply. “Dean, will you... now?”

“Let me just get us situated first,” Sam says. “Come here.”

Sam rolls to his back, pulls Cas on top of himself, and helps the angel get to his knees so he's straddling Sam. Then the taller Winchester pulls Castiel down for a kiss, and plants his own feet on the mattress, spreading them.

Castiel is effectively spread out on top of Sam like a buffet for Dean's taking, draped over the taller man's chest and stomach, ass up and spread open.

“Should I not be able to see Dean's face during intercourse?” Castiel asks, looking back over his shoulder.

“Next time,” Sam soothes. “This position will be easier on you.”

“I am pleased you will invite me again,” Cas says, and gives Sam a rare smile. “Now please tell your brother to start sodomizing me.”

Dean, a helpless chuckle bubbling up from his chest, climbs onto the bed on his knees and shuffles up to Cas. Laid out like that, Sam's legs holding the angel's own wide apart, Dean's younger brother's big hands on that pale skin, Cas looks more beautiful than he ever has. Dean feels his heart hammering in his chest and spares a brief moment to wonder how he can love two people so much.

Well, a person and an angel. Maybe that explains it. Not really two people, is it?

“Dean, come on, dude,” Sam urges, and Dean snaps out of it. He rolls on a condom and applies lots of lube. Nothing is going to ruin this for Castiel, absolutely nothing.

“You ready, Cas?” he asks, running his hands down those slim hips. “You good?”

“Yes,” the angel says, and it's so open, so honest. “Yes, I want this very much. I will tell you if I do not like it.”

Dean holds himself steady and begins pressing into Castiel. The angel's opening is tight, his skin burning hot, and the air feels electric around them. Dean draws in a shuddering breath. Sam's hands rub soothing circles on Cas' back. Everything is still and tense for a moment.

“Oh,” Castiel says again. “Oh, that feels...”

“You okay?” Sam asks, and Dean hears the concern in his brother's voice.

Sam loves Castiel, too. Dean didn't know until now.

“Profound,” Cas groans, his face pressed against Sam's chest. “The word I wanted. This feels profound.”

“Like I said, weird dirty talk,” Dean says from between clenched teeth. He's trembling all over, he wants this so much. “We good?”

“Good,” Cas confirms, and wriggles a little. “Dean, I want more.”

Dean fucks Cas, then, there on that ratty motel bed. He puts his back into it and starts giving Cas such a thorough, deep fucking that the angel can only lie there, rocking against Sam underneath them and moaning.

“Dean,” Castiel moans. “Dean, Dean, Dean!”

Dean's eyes are about to roll up in his skull and he bites his lip hard to keep from coming already. “Cas, please, shut up!”

“No, it's fine, Cas,” Sam says, cupping the angel's face and pushing those dark strands out of his face. “He's just trying not to come too soon. Go ahead. Tell him.”

“I need... need to be touched,” Cas gasps. “Please. Sam, please.”

Sam immediately reaches between them and grasps Castiel's dick. Stroking the angel slowly, he murmurs, “Let yourself feel it, Cas. Show us.”

Cas cries out and comes all over Sam's stomach, and the clenching heat of his body forces Dean to stop lest he pops too soon. Castiel moans and presses his face into Sam's chest, gasps Dean's name and makes shocked little noises with every twitch. Sam feels the sticky heat of the angel's climax coat his own skin, and he can see Dean's desperate look over Cas' shoulder.

“You too, Dean, show me,” Sam says softly. “You've wanted this, right? Wanted this so long.”

“I love you,” Dean gasps, resuming his thrusts. “Love you, Sam, I swear, even if I love Cas too, I still...”

“I know,” Sam says, smiling now. “Dean, dude, stop trying to turn this into a marathon event, just give in already.”

Dean does. He gives a hoarse shout and he tenses up all over and he comes, spectacularly, into Cas. He shudders and gasps as it rolls over him, and Sam's heart clenches. Dean has been wanting this, feeling guilty about it all the time, for ages, possibly months. Sam wants his brother to have everything, including another man, if Dean can just feel like he's obviously feeling now, forever.

“Oh,” Castiel says, sounding surprised, and lifts his head to meet Sam's eyes. “I can feel... everything.”

“Cas,” Dean groans, then slowly pulls out of the angel, gentle and careful with him. “Cas, c'mere.”

Cas turns his head around so that Dean can kiss him. They're both kind of lying on top of Sam now, and even with his advantage in size, it's too heavy. Also, Sam hasn't come yet and he's uncomfortably hard. He needs them to let up so he can take care of himself.

“Dean, let him up,” Sam moans. “C'mon, dude, I need -”

“Will you also sodomize me?”

Dean and Sam both stop everything and stare at Castiel for a few moments. Then Dean backs up and deals with the condom while Sam helps Cas roll off and sit back, and then they're all three of them sitting on the bed, two of them staring at the third.

“What, now?” Sam asks, stupidly. His dick is still hard.

“Yes, I think it would be best to take advantage of my post-coital relaxation,” Castiel confirms.

“You, uh, you didn't get enough that first time round?” Dean asks, trying so heartbreakingly hard for nonchalant, but Sam can hear how devastated he'll be if he didn't satisfy Cas.

“Oh, yes,” Castiel says, sounding pleased. “That was very enjoyable, Dean. Thank you. But Sam has not yet achieved orgasm, and I thought it would be unfair to him if he did not also have the opportunity to sodomize someone. I know you do not allow it, Dean, so I am offering.”

Dean looks murderous. “Hey, that is not – I am not _not_ allowing anything! It's just... I mean... Tell him, Sammy!”

“Cas, I don't have to,” Sam says soothingly. “Dean and I tried that, it didn't work out for us. I mean, don't get me wrong, I'd love to have you like that. But things don't have to be, uh, fair like that when we're having sex.”

“But I would like to consummate our new relationship,” Cas says hopefully. “I love Dean and I have copulated with him. I find that I also love you and I would like to copulate with you also. I think you should sodomize me now.”

Sam laughs. Cas, while seeming human in many ways, will never be completely convincing, and Sam loves it. Dean does, too, for all his posturing about Castiel's terrible dirty talk.

“So, uh, just to be sure,” Dean asks, “it was good. Us, I mean. You're not asking because I wasn't... good enough.”

“No, you were excellent, as evidenced by my ejaculating on Sam,” Cas confirms.

“Dude,” Dean says helplessly, but Sam is getting more and more interested.

“So... I could just fuck you right now? You're still loose from Dean?” he asks, giving himself a few tugs to keep it up for Cas.

“I would enjoy that,” Castiel confirms, and gets to his hands and knees. “Should I also position myself like this for you?”

“Yeah,” Sam says, then reaches for a condom. “Yeah, Cas, on your knees, like that. Dean, get in front of him.”

They switch places, but this time Castiel is holding himself up and Dean is sitting in front of him, kissing him with all the enthusiasm of a fourteen-year old with his first boyfriend. Sam loves seeing them together like this, but then Castiel arches his back and shows Sam what he's being invited to do. Where Cas wants him.

Holy fuck.

Sam rolls on a condom so fast he's barely sure it doesn't tear. He carefully slides his fingers into Cas and finds him still slick, still loose. The angel groans and rocks back, moans that he wants it, and that draws an echoing groan from both Winchesters. Holy hell, an angel begging for his cock? Sam's harder than he can ever remember being. He gets to his knees behind Cas and lines up.

“Deep breath for me, Cas,” he reminds the angel, and just as Castiel starts exhaling, Sam pushes in.

“Oh!” Castiel breathes, and his hands tighten on Dean's forearms. “That is... more intense. I... I think... ow.”

Sam stops immediately. “Cas, are you okay? I'll stop. We can do... something else.”

“No, I want this,” Castiel insists. “Wait, let me...” A tingle runs over Dean and Sam, telling them the angel just used his mojo. “There. I'm ready. Go ahead now, Sam,” he says, sounding smug.

“Wait a minute!” Dean insists. “Are you telling me you just used your angel mojo for _this_? Seriously? You just abused your heavenly privileges for gay, incestuous sex? Aren't they gonna kick you out for something like that?”

“Heaven does not keep score of things like these, Dean,” Castiel corrects him. “I am free to use my powers as I see fit. And now I see fit to use them to allow Sam to take me despite his uncomfortably large -”

“Oh God, shut up!” Dean groans, covering his eyes. “Seriously, Cas, what the hell?”

“Castiel,” Sam says, and his voice is deep and soft. “Do you want me to keep going?”

“Yes, Sam. I want you to take me like Dean did.”

Sam grips the slender hips in front of him and begins moving in and out. Cas exhales shakily and begins pushing back into it. Dean, still wide-eyed over Cas' tricks, is staring at his younger brother with open wonder in his eyes. And Sam revels in it.

He's never taken Dean like this. He experimented, once or twice, while he was at Stanford, but he's never been balls-deep in another man like this before. His body knows what to do; he's been fucked enough to know how to take care of a partner from the other end, and it's mostly like fucking a girl. But what's new, what's unique, is the look on Dean's face, the intense heat of Cas' angelic body, the scent of the three of them together. The feel of strong, masculine musculature under his hands as he fucks forward into another body. The deep, whisky-voiced groans coming from Cas at every thrust.

“Fuck, Sammy, you should see yourself,” Dean breathes, then looks down at Cas and buries a hand in the angel's hair. “He looks so good in you, Cas. Christ, you should see him, see how powerful he looks fucking you. How big he is next to us.”

“Tell me,” Cas gasps, and grabs Dean's shoulders to steady himself. He rocks against the hunter with every move. “Show me with words.”

“His shoulders,” Dean describes, looking back at his little brother. “They're all bunched up and tight. His chest, too. He's holding himself back, Cas; he's trying not to hurt you. Is he too big? Can you even take it?”

“Barely,” Cas rasps, and Dean feels a stab of heat low in his gut. “I'm... on the edge of pain.”

“And his eyes are darker than usual,” Dean narrates, then leans in to give Cas a brief kiss. “His hands are a lot more tan than your ass. They look so good holding you in place. Letting him drill into you. Are you getting hard again? I know I am.”

“Yes,” Castiel confirms, a sound far more moan than speech. “Yes, Dean, I... I need you to touch me again.”

“Cas,” Sam warns. “Cas, I can't wait, I've been... I'm too close.”

“Then come for us, Sammy,” Dead coaxes, stroking slowly over Cas' shoulders and back. “We'll save it for round two. Come on, give it to Cas, fill him up good. He wants you to.”

“I want you to,” Cas echoes on a groan. “Yes, Sam, please.”

Sam bites his lip and thrusts again, keeps going, pushing towards orgasm. He's close, he's been desperate for what feels like hours, and fucking someone for the first time in years is overwhelming. He tightens his hold on Cas' hips.

“Dean,” he gasps as he feels the first shudders overtaking him. “Cas!”

Sam comes hard, gasping for breath, and Dean stares at his magnificent little brother as if seeing him for the first time. Cas pants into Dean's clavicle. Sam looks hotter than Dean has ever seen him, and it's all because he's fucking someone, finally getting to feel that.

Dean is, suddenly and inexplicably, intensely jealous of Cas. As Sam comes down from his high, heaving for breath and stroking those ridiculously big hands down Cas' sides, Dean realises that it should have been him. Not because he doesn't want Castiel to have it, but because Sam's first time fucking another man? That should have been Dean underneath him. Every other first in Sam's life, Dean has been part of. Hell, Dean has been Sam's first since that first time Sammy had sex, because it was Dean who taught him how.

But Dean has never been able to do that for Sam and suddenly, it feels all wrong for Castiel to know what it's like being fucked by Sam when Dean only knows he's never managed that.

“Sammy,” Dean says, voice unsure. “Hey, uh, you wanna... try that on me sometime?”

“What?” Sam asks, confused. “Talking you through it while you're fucking Cas? Pretty sure we just did that, like, a half hour ago.”

“No, dude, I mean... You know. Topping. Do you want to, uh, switch it up? Sometime. Not now, obviously, since you just, uh, finished,” Dean stutters, and he knows he sounds like he's not man enough to talk about things like an adult, but it's just, well, embarrassing. Him and Sam have been fucking for ten years and _now_ he wants to try switching? It sounds pretty lame, even to Dean.

“Dean,” Sam huffs, still breathing heavily. “Just because Cas did that angel mojo thing doesn't mean you have to force yourself to do something you don't want to. We tried, remember? It's fine.”

“No, but I want to,” Dean says, and realises he sounds like he's begging. “I mean, if you don't, sure, fine, but... I was thinking, if Cas can mojo himself through it, why not me, right?”

“Are you two debating whether or not it will be possible or advisable for Sam to be on top?” Castiel asks, but his lips are mashed against Dean's skin so it takes a little time for the Winchesters to understand him. “Aren't you tired?”

“Well, now, yeah,” Sam agrees, then leans down to kiss Castiel's shoulder before gently pulling out. “I'm gonna crash for a while. You?”

“I don't think that sounds pleasant,” Castiel says, confused.

Dean chuckles. “Sleep, Cas. We're taking a nap. C'mere, lie down.”

“We are all partially covered in bodily fluids,” Cas objects. “I will remove the mess.”

And he does, with one wave of his fingers. The bed, their skin, everything is suddenly clean and dry. Then Cas carefully pushes the covers down. “We should cover up. Humans get cold very easily.”

Sam and Dean join him, Cas in the middle, and pull the covers back up.

“Wait,” Castiel says, and sits back up. “I should be on one side of the bed. Otherwise I can't watch you both.”

“Creepy,” Dean says, but it's fond and he's smiling as he speaks.

“Angels do not sleep,” Castiel reminds him. “I do not, as you say, crash. But I would very much like to stay all the same. I will watch over you and alert you should anything happen.”

“Yeah, sure, Cas,” Sam says, grinning. “Here, climb over.”

Castiel climbs over Sam and settles on one side of the bed. Sam grabs Dean and pulls his brother close, and Dean settles comfortably with his head on Sam's massive chest. The lights turn out. This is turning into the best day ever.

“And when you wake up, we can discuss this switching,” Castiel says in the darkness.

***

When they do wake up, Dean feels disoriented for a moment since there is human warmth on both sides of him. He's used to waking up plastered to Sam, but the extra presence throws him for a moment until he remembers last night. Or earlier this night. Or whatever, he has no idea what time it is. There's no light coming through the curtains, but then, the curtains and blinds do keep out most of the light anyway.

“Look who's finally awake,” Sam says, and Dean looks up. His brother is grinning down at him, looking unbearably smug. “Sleep well, princess?”

“Shut up, Sammy,” Dean grouses good-naturedly. He turns his head to see Cas staring intently down at him on his other side. “I thought you were over there.”

“I moved around as you slept,” Cas explained. “I only recently got back into bed.”

“Uh-huh. So, breakfast,” Dean mutters, rubbing at his eyes.

“It's closer to lunch time, actually,” Sam says, and when Dean looks at him again he can see the hunger in his younger brother's face. “So, uh, food first? Then back here?”

It takes Dean's sleep-addled brain a moment to understand what Sam is hinting at, but then it clicks. He can feel his own face going hot. “Uh, yeah, I mean... or... I guess?”

Sam's face pinches a little. “Dean, if you've changed your mind... I mean, we don't have to.”

“No, no, I wanna,” Dean says immediately, trying to reassure his younger brother. “I do! It's just, you know, with... with Cas and everything...”

“Do you not want me to be present for the popping of your cherry?” Castiel asks.

Sam howls with laughter.

Dean pulls a pillow over his face. “Cas, I swear, the worst dirty talk I've ever heard! It's embarrassing!”

Cas frowns a little. “But my question remains unanswered. Am I not welcome for this?”

“Dude, if you're not here to mojo me through it, it's not even happening,” Dean says, and then, hesitantly, puts a hand on Castiel's shoulder to pull the angel a little closer. “Is that okay? With you, I mean. You want in?”

“I believe I would like to join in all of your incestuous activities in the future, if I am indeed invited,” Castiel says, and he's smiling slightly. “I enjoyed it very much.”

“You're invited,” Sam says firmly. “Dean's wanted to ask you for a long time, he just didn't think I'd be okay with it.”

“Dude, why do you have to tell him that?” Dean complains.

“I want him to know that this isn't some bad idea we got while drunk,” Sam explains. “Cas, we want you with us. If you're okay with us being together like this, me and Dean, then we're happy to have you join us. We care about you.”

“This is all very gratifying,” Castiel says happily. “Now we should secure pie for Dean, so that he will have the energy to be sodomized for the first time.”

They go to a nearby diner, and it really is lunch time. They get a burger for Dean, a chicken salad for Sam, and a milkshake for Castiel, since the angel would look strange just sitting there and has also never tried a milkshake while in human form. They eat and talk among themselves as if this was just another normal day, but then Dean offers to get the pie to go so they can go back to their motel room.

“All fuelled up,” he says, giving himself two thumbs up.

“Actually, let's get a whole pie,” Sam says, eyes going darker than usual. “I think we'll need it.”

The waitress stares at them when they order a whole pie with three forks to go, but Dean looks so incredibly boyish and happy that she can't resist his charm.

“We only have cherry today, is that okay?”

Sam doubles over laughing. Castiel even gives a tiny smile. Dean, his turned ears furiously red, pays for the pie and accepts the tin foil covered pie dish when the waitress holds it out. They make their way back to the motel, Sam sniggering the entire way.

“Shut up, Sammy,” Dean grouses again.

“It is very amusing,” Castiel pipes up. “That we are about to pop your cherry, and the diner serving only cherry pie.”

“Where did you learn that stupid phrase, anyway?” Dean grumbles.

“I read it in a magazine once,” Castiel easily replies. “It is a common phrase, isn't it?”

“Your face is common,” Dean mutters, but even as he says it, he knows it's not true. Castiel's face is, quite literally, heavenly.

They make it back and inside the door before anything else is said. Dean carefully places the pie on the table, Sam carefully closes the blinds, and then Castiel becomes impatient. The flutter of wings is the Winchesters' only clue that he is using magic; that and the cold draft as they suddenly find themselves naked.

“Whoa, there,” Dean says, gasping as cold air touches all of him at once, unexpectedly. “Slow down, Cas, we're not in a hurry.”

“It feels as though I have been waiting for this since I pulled you from Hell,” Castiel says, and his voice is suddenly a lot more intense. He is also naked. “For you two, for this... this profundity. I was always meant to end up here, with you. I do not want to wait.”

Sam smiles at the angel, then walks up to him and dips his head for a kiss. “I know what you mean. Want to help me prep Dean the old-fashioned way before you mojo him ready?”

“Sure he does,” Dean says, false bravado coming off him in waves as he throws himself nonchalantly on the bed. “Who'd say no to getting their hands on all this?”

He gestures to himself and lies back, stretching, making a show of it.

“You must prepare him as he usually does you,” Castiel says, joining Dean on the bed but addressing Sam. “So I can learn. Then I will help with the rest.”

Dean swallows nervously as Sam gets on the bed with them, a tube of lube in his hand. “Yeah, sure. Get to it.”

“Dean.” Sam's voice is softer than it usually is when they're having sex. “Are you sure? Absolutely sure?”

Dean rolls his eyes. “Shut up and fuck me, bitch.”

“Jerk,” Sam says warmly, nosing up along Dean's throat. “Spread your legs.”

Dean is taking slow, measured breaths, carefully not hyperventilating, but the other two men notice. Of course they do – they know him.

“Cas, you should kiss him,” Sam suggests with a grin. “Distract him a little.”

Dean is about to make a snarky reply when Cas' lips find his. The angel hasn't lost that lightning taste, the sense of electricity running through Dean's entire body as they kiss. Dean pushes a hand into Castiel's hair and angles his head a little so he can deepen the kiss. Castiel enthusiastically pushes his entire tongue into Dean's mouth.

Then a finger is sliding into Dean's ass and he takes a deep breath. He breathes all the air right out of Castiel's mouth, and the taste of milkshake lingers.

“I'm going to put my fingers in him,” Sam says, and his voice is gritty with lust. “See, Cas, one first, then two, and so on until he's ready.”

“When will you know he is ready?” Castiel asks, sounding genuinely intrigued.

“Sammy usually begs for it, but that's not really my style,” Dean tries to brag, but then Sam slides a second finger into him and he makes a strangled noise at the end of that sentence.

“I usually have to tell you to get the hell on with it, since you're so freaked about hurting me,” Sam huffs. “So, yeah, usually I tell him when I'm ready. But he's never been ready before, so I guess I'll be the judge of that, huh?”

Castiel nods. “When his muscle is loosened enough for you to insert your erection.”

Dean groans into Cas' neck. The angel is lying on his side next to Dean and is providing an excellent place to hide Dean's face when he says something too cringe-worthy. That, and he smells amazing. Oh, and his skin is hot and sweaty and Dean wants to lick it all over. Dean runs his hand down Castiel's side and over his hip, then gently grasps hold of the angel's erection.

“You, uh, you wanna try being on top sometime, too?” Dean asks as he strokes.

Castiel moans, loudly and shamelessly, and bucks into Dean's grip. “Oh, yes.”

“Maybe we should, uh, start with the two of you,” Sam says, and Dean's eyes snap up to his face. “I mean, no offence, Cas, but I'm a lot bigger than you. It might, I don't know, be easier to start with you.”

“What, you don't wanna do this?” Dean demands, and even he can hear how affronted he sounds. _Calm down there, big brother. Stop acting like Sam just told you he's really not that into you._

“Dean, I want this more than I've wanted anything in my life,” Sam says, and suddenly all the air is gone from the room. Dean sucks in a breath. “You know what this means to me. You know how messed up I've been over you my _entire life_. But I'm not gonna force it. We tried this before, remember? I'm just saying. Cas might be... easier.”

“With a little help, I don't think it will matter,” Castiel says conversationally. “I would like to sodomize you, Dean, but I understand this first time must be Sam's doing. I will assist to make sure you enjoy it.”

“Everyone, stop talking,” Dean grumbles. “Jeez, just tryin' to make sure. Okay, I'm good. Giddy up.”

Sam snorts. “I have two fingers in your ass, Dean. You really think that's going to do the trick?”

“Well, Cas'll take care of it, right, Cas?” Dean says dismissively. He wants to start fucking so Sam will stop talking. His little brother always gets so intense with his sharing. Dean never knows how to tell him that he feels the exact same way.

“Not yet,” Sam decides, and pushes another finger into Dean. “I want to enjoy this.”

“Jesus,” Dean pants. “That... that's tight.”

“You okay?” Sam asks, and he puts a hand on Dean's hip. “Need me to stop?”

“Nah, keep going. Just, uh, could you get some more slick?”

Castiel, ever helpful, leans over Dean to hand Sam the lube. When Sam's fingers are slick enough to make squelching noises going in and out, the angel moves so he can see better. Dean feels intensely embarrassed when he catches sight of Castiel's deeply focused frown aimed directly at his own groin.

“He seems loose enough,” Castiel comments, but Sam shakes his head.

“We've tried this before, remember? Twice. He looks like he's ready, but I can feel him tensing up just thinking about getting fucked.”

“Dean, this does not sound pleasant for you,” Castiel says, and he sounds worried. “Why are you forcing yourself to go through with this when you do not enjoy it?”

“I do enjoy it,” Dean insists, but then he squeaks as Sam's fingers press deep. “Holy fuck!”

“Wait, just give me a second,” Sam mutters, moving a little, and then -

“Christ!”

Sam grins. That's not pain straining his brother's voice. That's the sound of a man trying very, very hard not to come. That's the sound of a man having his prostate firmly rubbed by three fingers.

“Sammy,” Dean gasps, writhing on the sheets. “Sammy, Sam, Sa-”

“If I suck you now, can you hold it until I fuck you?” Sam asks, slowly shuffling down backwards on his knees.

“Yeah, yeah, just -” Dean rambles. Then his voice dies away into a hoarse groan as Sam puts his lips on his brother's dick and sucks.

“Fuck, fuck, fuck,” Dean mutters. He clenches the sheets in white-knuckled fists and does his level best not to just come already. Wants so desperately to shoot down Sam's throat, fuck his brother's expressive mouth and come all over it. It's so good; the heat, the saliva, the huge hand still fucking him on three fingers.

“Surely he is ready now,” Castiel says, and his voice is urgent and desperate. “Please, Sam, let me see you take him. I will make sure it does not hurt him.”

Sam pulls his mouth off Dean's dick and grins up at the older Winchester. “What do you say, Dean? You ready to have your cherry popped?”

Dean tries glaring, he really does, but Sam's fingers are still pressing on his prostate and the only thing he can manage is a gargle. Sam's grin widens and he slowly pulls back.

“Cas,” he tells the angel, looking at Dean like the little fucker he is. Figuratively speaking, of course. In reality, Sam is an absolutely huge fucker. “Cas, c'mere, put your fingers in him. Keep him stretched for me.”

Cas does so almost too eagerly. Dean sucks in another breath at the feeling of Castiel's fingers sliding in almost before Sam's are out. The angel slides his fingers slowly in and out, watching Dean with that intent blue gaze the whole time. Sam puts on a condom and adds more lube, then moves back over Dean.

“Hand me a pillow,” he tells Cas, who quickly complies. “Dean, lift your ass.”

When the angel pulls away, Dean suddenly feels the loss of those fingers. Then Sam is back, pushing his own fingers in and rubbing, stretching. Dean's hips are tilted up by the pillow, Sam is lying over him, and Castiel is pressed up against his side.

“Hey, Dean?” Sam says, placing his dick against Dean's opening. He gives a little push and the head of his dick slides in.

“Sa-a-aaam,” Dean whimpers.

“You know I love you, right?”

Dean closes his eyes tight. “Nnghyeah. Same.”

There's a whispered phrase above his head, but Dean can't focus on anything but the feeling of a huge dick in his ass. It's not, so far, a bigger success than the last time they tried this. He opens his mouth to take a deep breath, and suddenly, his whole body relaxes. He sinks into the mattress. Sam sinks all the way into him. He can even feel his frown evening out. Warmth ripples over his skin.

“Oh God,” Sam gasps, and Dean can feel his huge brother pressed against almost everything. Everywhere. “Dean, God, did you feel that?”

“Yeah,” Dean sighs dreamily. He slides his hands up Sam's arms. Huge arms. Bulging freaking biceps. “Yeah, Sammy.”

“Fuck,” Sam groans, leaning his forehead against Dean's for a moment. “Fuck, fuck, fuck...”

“Are you in any pain, Dean?” Castiel asks, then leans in to place a little kiss on Dean's lips. Just a friendly little check-in, almost. “Do you need me to do more?”

“Cas,” Dean murmurs, pulling the angel down for another kiss. “Don't you dare. This is friggin' perfect. What did you do?”

“I merely loosened all your unnecessary muscle tension,” Castiel says, then leans in for more kisses. “You were nervous. You are not anymore.”

“He's so tight,” Sam gasps, rocking a few inches back and forth. “Cas, c'mere, feel this.”

Then he grabs Castiel's wrist and pulls the angel's hand down between Dean's legs. Dean can feel his face go hot as Castiel's fingers slide around where he's being split open on Sam's dick. That little touch feels so strangely intimate.

“You feel divine, Dean,” Castiel breathes, eyes fixed on Dean's face. “I am looking forward to when you will let me take you.”

“Speaking of,” Dean rasps, “today, Sammy. Come on.”

Sam's shoulders bunch again, and Dean is so happy Sam decided to have him on his back rather than on his knees. It's important he sees Sam for this. He needs to watch his magnificent little brother as they fuck this way around for the first time. And knowing Sam, he probably knew that Dean would need that. Dean feels heat suffuse him as he watches Sam put his back into it and _thrust._ Then his eyes roll up in his head and he can't see very well any more.

“God _damn_ ,” Dean gasps, sliding his legs up around Sam's waist as far as he can get them. “Sammy, holy shit, what even...”

“Yeah,” Sam agrees, face red and sweaty with exertion, his muscle straining as he rolls long and slow into his brother, arms keeping his weight off. “Yeah, fuck, Dean!”

The sensation is intense, bordering on painful, and just the right side of it to make it even hotter. Little Sammy – huge, freakishly monstrously big Sammy – is really going at it, thrusting into his big brother with such slow, deep slides Dean has long since lost the ability to form intelligible sentences. Dean is reduced to groaning and gasping for breath, his eyes slipping shut and then fluttering open again as he tries to focus on Sam.

“Fuuuck,” Dean exhales.

“Yes,” Castiel agrees. “You certainly are.”

Sam barks out a laugh and his hips stutter. Then he leans down to kiss Dean and for a short moment, they breathe the same air before their lips meet. Sam is tall enough to keep fucking Dean even as they kiss, and goddamn, isn't that all kinds of hot?

“So hot,” Dean confirms even though he's mostly talking to himself.

“Cas, help us out,” Sam pants, still keeping up that slow, deep motion. “Give Dean a hand.”

Sam raises himself up a little more so there's room between them. Cas, eager and curious, grasps Dean's erection in his hand and starts stroking experimentally. This makes Dean moan and that, in turn, makes Sam need to bite his lip to stop from just coming all over everything.

“Perhaps,” Cas says hopefully, and his gaze flits between the two brothers, “I can also try being on top. Next time.”

“We'll do a spitroast,” Sam gasps. “You can fuck me while I suck Dean.”

Dean lets out a sharp yelp when Sam, riled up by the thought of being spitroasted between his brother and their angel, pushes a little too hard, a little too fast. Sam stops, but even as he stops his hips are stuttering as if it's physically impossible for Sam not to fuck forwards into Dean.

“You okay?” he asks, looking down at his older brother with concern.

“Little slower, Sammy,” Dean grunts, straining up to get them moving again. “Keep going, just go slow.”

“Hang on,” Sam says, and then he's getting his knees under him, sitting up straight, and picking Dean's right leg up to rest his ankle over Sam's shoulder.

“Whoa,” Dean starts protesting, but then Sam starts thrusting and jerking him off at the same time, everything tightens, and all thoughts of protest go shooting out Dean's dick in an orgasm so sudden it shocks him. He writhes and arches up into it and moans their names, coming harder than he has in his life.

Except the first time he ever got to fuck Sam, but what can you do, early twenties dicks have their own parameters for excellence.

“Wow, Dean, that does it for you, huh?” Sam asks, and he sounds so smug Dean is going to smack him, he is, he just needs to stop writhing with how good everything feels first.

“Shut up,” Dean mutters, thrashing a little.

“Hang on,” Sam says again, then braces against Dean's raised leg and starts thrusting hard again.

It hurts.

“Ow,” Dean whimpers. “Uh, Sam, ow.”

Sam stops, but the sound of frustration he makes is painful to hear. “Too much?”

“Sensitive,” Dean explains apologetically. “Sorry, dude, I just can't.”

“I could assist,” Cas offers, and Dean looks around to meet the angel's eyes. He'd almost forgotten Cas was there. “I could – temporarily – numb your soreness. Permanently, if you wished.”

“Cas, no, it's fine, I can just -” Sam starts, but Dean is not having any of that self-sacrificing shit if there is an easy solution within reach.

“Like, all of it? Numb?” Dean asks, putting a hand over Sam's mouth to make him shut up.

“Yes,” Cas agrees, then touches Dean's forehead and suddenly the hunter can't feel anything from the waist down to the knees.

“Whoa!”

“Now please, Sam,” Castiel says, and his eyes are dark and hungry. “Finish it. I want to see you complete. Together.”

“Sammy,” Dean murmurs, reaching up to push Sam's ridiculous hair out of his eyes. “'s a miracle, I can't feel a thing. Fuck away, dude. Go nuts.”

Sam laughs again and Dean can't get over how good it is to hear that sound. To see Sam's perversely wide shoulders shaking with laughter. “Dude. An angel just gave you local anaesthetics so I could fuck you right. How is this even our lives?”

“Karma,” Dean suggests with a grin. “After all the shit we've waded through, it's payback time. All-access pass to all the sex we can think of. Right, Cas?”

Cas doesn't reply, seeming confused, but he leans in to kiss Dean chastely and Dean immediately opens his mouth to make the kiss deep and dirty. Sam rolls his eyes, but he pulls out a little and pushes back in a fraction, testing his brother's response.

Dean just wriggles against him. Okay then.

Sam clenches his jaw and moves into short, sharp thrusts to chase his own pleasure. The wet drag of the lube, the tight muscle around his cock, the sight of Dean and Cas making out right in front of him are all little tongues of fire dancing over his skin. All together they're almost unbearable. He's so close to coming he can feel his balls drawing up, his skin itching with it. He kisses Dean's ankle and tightens his grip on Dean's leg. So close.

“C'mon, Sammy, give,” Dean says, lips still catching on Cas', and looks up with a dirty grin. “'S go time.”

Sam laughs again, taken by surprise with it, and he loses focus and Dean clenches down and – yeah. Hissing out unintelligible syllables between clenched teeth, he bucks his hips into Dean again and again as orgasm shorts his brain out, drawing everything he is out and into the older Winchester grinning up at him. Sam collapses onto his brother, shaking with pleasure and exhaustion and sensory overload.

“Wow.”

“I know, right? Dude. Angel mojo. Who knew?” Dean says on a chuckle. “Hey Cas, what else can that mojo do? Could you give yourself, like, a set of boobs if you wanted?”

Sam snorts into Dean's chest.

“I... why would I do that?” Cas asks, sounding honestly perplexed.

“Well, because boobs. There's no wrong time for boobs, ever,” Dean explains, but he's running a hand slowly through Sam's hair and his voice is lazy. He doesn't really care about the boobs.

Cas looks pensive. “I do not think altering my vessel is within my power on this plane. Nor is altering your bodies. I can, however, heal or numb us as is required. I might be able to induce orgasm, but that would require experimentation.”

“Great, we'll, uh, experiment next time,” Sam grins, raising his head to look at Dean again. His brother has this soft look that Sam almost never sees anymore. “And Cas? Thanks. For helping out.”

“Yeah, thanks for making sure Gigantor here could finally tap some ass, what a loser,” Dean jokes, ruffling the long hair between his fingers.

“At least it doesn't take angel mojo for me to man up enough to take it up the ass, huh, big brother?” Sam snarks back.

“Shut your pie hole,” is the grumpy reply. “And also, get your Frankenstein dick out of my ass already, before you do permanent damage.”

“You know Frankenstein wasn't the monster, right?”

“Sam. Dean,” Cas cuts in, a little louder than he normally is. “You're both welcome. Now be quiet. I have never enjoyed post-coital cuddling before, and I wish to enjoy it without your bickering.”

Dean sniggers, Sam pulls out and goes to deal with the condom and get Dean a wash cloth. When Sam gets back, Castiel is spooning Dean (who will never say so but who absolutely loves being the little spoon) and Dean is almost asleep already.

“Okay if I get in behind you, Cas?” Sam asks, just to be sure. Castiel might need to watch them both again.

“Yes, I will enjoy that. Being in the middle is extremely gratifying,” comes Cas' gravelly voice in reply.

“My turn in the middle next time,” the younger Winchester says, and gets in the bed. He pulls the covers up. “For that spitroast.”

They all settle in, cuddle close, and Sam is just about to doze off when it hits him. He kisses the shoulder in front of him. “Hey, Cas. You didn't... did we forget you? I'm sorry.”

“No, I achieved orgasm simultaneously with Dean,” the angel says, surprising Sam. “Watching you was also very gratifying. I took care of the mess. My grace can be very helpful with messes.”

Sam chuckles. “Well, that's good, then. Dean, you hear that? We're gratifying to watch.”

Dean snores at him, and Sam gives up getting a response out of his brother. He tucks his face against Castiel's shoulder and breathes in the scent of the three of them. The bed is going to be way too hot in a little while with all three of them like this, but for a moment it's absolutely perfect.

“Hey, Sam?” Dean murmurs, the sound barely audible.

“Yeah?”

“Think we can do this again sometime? Like, tomorrow maybe?”

Yeah. Perfect.


End file.
